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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1965101Generated: October 25, 2026

Hydrochloric Acid → 6-Bromo-2',3',5',6'-tetrahydrospiro[indene-2,4'-pyran]-1(3H)-imine

https://huagongshe.com/reaction/1965101

Reaction equation

Participants

RoleNameHCIDCharge
ReactantHydrochloric AcidHCID 313—
ReactantDiethyl EtherHCID 3283—
ReactantN-(5-Bromo-2',3',5',6'-tetrahydrospiro[indene-2,4'-pyran]-3(1 H)-ylidene)-2-methylpropane-2-sulfinamideHCID 67979409—
Solvent1,4-DioxaneHCID 31275—
Product6-Bromo-2',3',5',6'-tetrahydrospiro[indene-2,4'-pyran]-1(3H)-imineHCID 67979506—

Reaction Steps

HCl (4M in 1,4-dioxane) (0.683 mL, 2.73 mmol) was added to a solution of N-(5-bromo-2′,3′,5′,6′-tetrahydrospiro[indene-2,4′-pyran]-3(1 H)-ylidene)-2-methylpropane-2-sulfinamide (Example 25 Step 1, 105 mg, 0.27 mmol) in anhydrous 1,4-dioxane (1 mL) and the resulting mixture was stirred under a nitrogen atmosphere at r.t. overnight. Et2O (3 mL) was added, the precipitate was filtered off, washed with Et2O and then dissolved in DCM (5 mL) and sat. aq. NaHCO3 (5 mL). The mixture was poured into a phase separator, the organic layer was collected and concentrated to give the title compound that was used in the next step without any further purification.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08415483B2
Source datasetuspto-grants-2013_04
ORD IDord-fa0048aae2a54fe08dbb19d6d2c2682d
Source noteuspto-grants-2013_04